Tris(trimethylsilyl)silane as a Reagent for the Radical Deoxygenation of Alcohols

Dietmar Schummer; Gerhard Höfle

doi:10.1055/s-1990-21219

Synlett 1990; 1990(11): 705-706
DOI: 10.1055/s-1990-21219

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Tris(trimethylsilyl)silane as a Reagent for the Radical Deoxygenation of Alcohols

Dietmar Schummer^* , Gerhard Höfle

^*GBF, Gesellschaft für Biotechnologische Forschung mbH., Abteilung Naturstoffchemie, Mascheroder Weg 1, D-3300 Braunschweig, Germany

Abstract

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The reaction of Barton and McCombie was improved by the substitution of tributyltin hydride with the new reagent tris(trimethylsilyl)silane for a smooth radical deoxygenation of cholesterol, lanosterol and 1,2:5,6-di-O-isopropylidene-D-glucofuranose, via the corresponding O-phenoxythiocarbonyl derivatives, without toxic tin-containing byproducts in the reaction mixtures.

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